After a year in amateur baseball, Chylak moved into the minor leagues as a
Pennsylvania-Ontario-New York League umpire. He spent several more minor league seasons in the
Canadian–American League, the
New England League, and the
Eastern League. He debuted in the major leagues in 1954. Chylak worked the first
American League Championship Series in 1969. On June 4, 1974, he was umpiring at third base in Cleveland for "
Ten Cent Beer Night". The
Cleveland Indians had been struggling with low attendance figures, resulting in this promotion that attracted more than 25,000 fans to the game. Fans became unruly and incited fights with the players, sometimes pouring beer on them. Chylak, exercising his authority as crew chief, declared the game a forfeit after he sustained a facial wound from being hit with a chair. After retiring from the field in 1978, he became an assistant league supervisor of umpires. Chylak was in the umpire's dressing room at
Comiskey Park on
Disco Demolition Night, a July 12, 1979, doubleheader between the
Detroit Tigers and
Chicago White Sox. Between the games of the doubleheader, unruly fans rioted. Because of damage to the field, the umpires, led by crew chief
Dave Phillips, refused to allow the second game to be played. When American League president
Lee MacPhail decided the White Sox must forfeit the second game, Chylak was the one who informed White Sox owner
Bill Veeck. According to family, his most memorable game was umpiring the 1960 World Series when, on October 13, Bill Mazeroski hit a home run off reliever Ralph Terry at Forbes Field in Pittsburgh. This was the only homer to end a World Series game 7 in major league history. With a total of 31 career ejections, he was also credited with never throwing Baltimore manager
Earl Weaver out of a game. ==Retirement==